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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-09-11 00:41:42 UTC
Update Date2021-09-14 15:20:06 UTC
HMDB IDHMDB0006938
Secondary Accession Numbers
  • HMDB0006781
  • HMDB06781
  • HMDB06938
Metabolite Identification
Common NameTartronate semialdehyde
DescriptionTartronate semialdehyde, also known as 2-hydroxy-3-oxopropanoate, belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. Tartronate semialdehyde exists in all living organisms, ranging from bacteria to humans. Tartronate semialdehyde has been detected, but not quantified in, several different foods, such as ginsengs (Panax), deerberries (Vaccinium stamineum), sourdough, prickly pears (Opuntia), and groundcherries (Physalis). This could make tartronate semialdehyde a potential biomarker for the consumption of these foods. Tartronate semialdehyde is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Tartronate semialdehyde.
Structure
Data?1582752415
Synonyms
ValueSource
2-Hydroxy-3-oxopropanoateChEBI
2-Hydroxy-3-oxopropanoic acidGenerator
Tartronic acid semialdehydeGenerator
Hydroxymalonaldehydic acidMeSH, HMDB
Tartronic semialdehydeMeSH, HMDB
Chemical FormulaC3H4O4
Average Molecular Weight104.0615
Monoisotopic Molecular Weight104.010958616
IUPAC Name2-hydroxy-3-oxopropanoic acid
Traditional Nametartronate semialdehyde
CAS Registry NumberNot Available
SMILES
OC(C=O)C(O)=O
InChI Identifier
InChI=1S/C3H4O4/c4-1-2(5)3(6)7/h1-2,5H,(H,6,7)
InChI KeyQWBAFPFNGRFSFB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Alpha-hydroxy acid
  • Hydroxy acid
  • 1,3-dicarbonyl compound
  • Monosaccharide
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Aldehyde
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility327 g/LALOGPS
logP-0.92ALOGPS
logP-1.2ChemAxon
logS0.5ALOGPS
pKa (Strongest Acidic)3.04ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.4 m³·mol⁻¹ChemAxon
Polarizability8.1 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+120.24331661259
DarkChem[M-H]-112.86831661259
DeepCCS[M+H]+125.05430932474
DeepCCS[M-H]-122.25730932474
DeepCCS[M-2H]-158.67330932474
DeepCCS[M+Na]+133.23630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Tartronate semialdehydeOC(C=O)C(O)=O2314.6Standard polar33892256
Tartronate semialdehydeOC(C=O)C(O)=O843.9Standard non polar33892256
Tartronate semialdehydeOC(C=O)C(O)=O1046.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tartronate semialdehyde,1TMS,isomer #1C[Si](C)(C)OC(C=O)C(=O)O1162.9Semi standard non polar33892256
Tartronate semialdehyde,1TMS,isomer #2C[Si](C)(C)OC(=O)C(O)C=O1077.6Semi standard non polar33892256
Tartronate semialdehyde,1TMS,isomer #3C[Si](C)(C)OC=C(O)C(=O)O1212.0Semi standard non polar33892256
Tartronate semialdehyde,2TMS,isomer #1C[Si](C)(C)OC(=O)C(C=O)O[Si](C)(C)C1227.5Semi standard non polar33892256
Tartronate semialdehyde,2TMS,isomer #2C[Si](C)(C)OC=C(O[Si](C)(C)C)C(=O)O1315.1Semi standard non polar33892256
Tartronate semialdehyde,2TMS,isomer #3C[Si](C)(C)OC=C(O)C(=O)O[Si](C)(C)C1287.3Semi standard non polar33892256
Tartronate semialdehyde,3TMS,isomer #1C[Si](C)(C)OC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1396.4Semi standard non polar33892256
Tartronate semialdehyde,3TMS,isomer #1C[Si](C)(C)OC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1305.1Standard non polar33892256
Tartronate semialdehyde,3TMS,isomer #1C[Si](C)(C)OC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1352.9Standard polar33892256
Tartronate semialdehyde,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(C=O)C(=O)O1405.6Semi standard non polar33892256
Tartronate semialdehyde,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(O)C=O1319.4Semi standard non polar33892256
Tartronate semialdehyde,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC=C(O)C(=O)O1479.3Semi standard non polar33892256
Tartronate semialdehyde,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(C=O)O[Si](C)(C)C(C)(C)C1663.8Semi standard non polar33892256
Tartronate semialdehyde,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)C(=O)O1788.5Semi standard non polar33892256
Tartronate semialdehyde,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC=C(O)C(=O)O[Si](C)(C)C(C)(C)C1734.8Semi standard non polar33892256
Tartronate semialdehyde,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1999.0Semi standard non polar33892256
Tartronate semialdehyde,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1886.9Standard non polar33892256
Tartronate semialdehyde,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1784.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tartronate semialdehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9000000000-a60f01ed6b22e180e0452017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tartronate semialdehyde GC-MS (2 TMS) - 70eV, Positivesplash10-00ac-9440000000-afd8c910b7b1f49d2e622017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tartronate semialdehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tartronate semialdehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tartronate semialdehyde 10V, Positive-QTOFsplash10-0a4r-9500000000-f812e132ac3b2e7366372015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tartronate semialdehyde 20V, Positive-QTOFsplash10-0a4r-9100000000-ceca81538df1215a85f72015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tartronate semialdehyde 40V, Positive-QTOFsplash10-0a4u-9000000000-9d63dd3b34de8e05e06e2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tartronate semialdehyde 10V, Negative-QTOFsplash10-0udi-6900000000-e9845cd50bf0a0e27a712015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tartronate semialdehyde 20V, Negative-QTOFsplash10-0pc0-9200000000-a8bdb790ea1f2037fb612015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tartronate semialdehyde 40V, Negative-QTOFsplash10-0a4i-9000000000-3b924f51c31faa2a9e9a2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tartronate semialdehyde 10V, Negative-QTOFsplash10-0zi3-9300000000-607c03f7e8cd6716e11d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tartronate semialdehyde 20V, Negative-QTOFsplash10-0006-9000000000-f440bef0a5740a66164c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tartronate semialdehyde 40V, Negative-QTOFsplash10-0006-9000000000-87a1803920534b6e560e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tartronate semialdehyde 10V, Positive-QTOFsplash10-0a4u-9100000000-46786392dfaa1185c6632021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tartronate semialdehyde 20V, Positive-QTOFsplash10-066u-9000000000-5de8c87d45a4af20988e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tartronate semialdehyde 40V, Positive-QTOFsplash10-0006-9000000000-034038c78b2eda187f412021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024155
KNApSAcK IDNot Available
Chemspider ID1090
KEGG Compound IDC01146
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1122
PDB IDNot Available
ChEBI ID16992
Food Biomarker OntologyNot Available
VMH ID2H3OPPAN
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Carbohydrate transport and metabolism
Specific function:
Catalyzes the reversible isomerization between hydroxypyruvate and 2-hydroxy-3-oxopropanoate (also termed tartronate semialdehyde) (By similarity).
Gene Name:
HYI
Uniprot ID:
Q5T013
Molecular weight:
30405.4
Reactions
Hydroxypyruvic acid → Tartronate semialdehydedetails